Over a 45-year career as a Chicago lawyer, chief executive and corporate director, Sheli Rosenberg executed enough big deals and took enough companies public to be deemed a superstar.

She also knew what it was like to be the only woman in the room, to be called a "little lady" and to be asked to fetch the coffee.

She reached corners roped off to many women while dedicating considerable time to paving the way for others. She was the only woman to lead a coed legal group in the country in the early 1970s and co-founded the Chicago Network, the city's pre-eminent group of female executives.

But enough was enough, even for an overachiever. Rosenberg, now 69, retired in 2002, tired and wealthy from her tenure working with real estate mogul Sam Zell, the city's richest man and chairman of the Chicago Tribune's owner, Tribune Co.

And then came an unexpected invitation.

In April 2010, Wayne Whalen of the law firm Skadden, Arps, Slate, Meagher & Flom asked Rosenberg to breakfast at the private Chicago Club. She thought Whalen, whom she had known since law school, was going to hit her up for a political donation.

Instead, he offered her a job.

"I looked at him like he was not feeling well. … It never entered my mind that I would ever consider doing something like this again," Rosenberg said.

Such an offer to a retired lawyer in her late 60s "is unbelievable; it's unheard of," said Kay Hoppe, a headhunter for law firms. "I would have said it was impossible, because very honestly, law firms are pushing people out at younger and younger ages. ... It tells you how powerful her potential contribution is."

This month, Rosenberg became "of counsel" at Skadden, a role akin to senior adviser. She plans to mentor young female lawyers, because "there aren't any senior women here," and to use her contacts to bring in new business. When asked whether her overtures would focus on the real estate sector, where she has the most experience, she replied: "My Rolodex doesn't say 'real estate' on it; it says 'Rolodex.'"

Hoppe called it "a genius move" on Skadden's part.

An 'old goat' before 40

Rosenberg grew up in Hartsdale, N.Y., the daughter of a treasurer of an X-ray company and a homemaker.

"My father approached the money he made as his money, and (my parents) would have terrible fights about $5," she said. "Somewhere along the way, I knew psychologically that I could never live in an environment similar to what my mother lived in and that I needed economic independence. I was never going to beg for $5."

Rosenberg attended Tufts University at a time when women still had curfews, and she started law school at Northwestern University after graduation. She was one of six or seven women in her class ofabout 150. The first female faculty member, Dawn Clark Netsch, did not join the school until Rosenberg's last year.

"One of the professors, in an almost sadistic way, taught criminal law by using rape cases and called on women extraordinarily frequently, given the population of females in the class," Rosenberg said. "It was a cruel thing to do for some women who were very uncomfortable under the questioning."

Another professor suggested in front of the class that if Rosenberg wasn't sitting in her seat, a man who was dying in Vietnam would be there instead.

She married Burton Rosenberg, a classmate, at the end of her first year of law school and had her first of two children the year after graduation, while an associate at a small firm.

"It was Memorial Day, and I assumed the office was closed," she said. "But I was the only one who didn't come to work. They worked around the clock, and I knew then it would be impossible to balance my work and my family there."

She left for Schiff Hardin, where she specialized in real estate law. She recalled having to write her own maternity leave policy, since there were few women, and no mothers, at the firm.

But Schiff allowed her to work from home in Highland Park two days a week. She made partner under that arrangement in 1973 and became the first female capital partner at Schiff about two years later.

At 31, she was the only woman in the country to head a legal group made up of men and women — the 1,500-member Chicago Council of Lawyers. The milestone got her a short write-up in a 1974 issue of People magazine.

While at Schiff, though, she felt lonely, "like a peculiar animal in a zoo that doesn't have very many of these kinds of animals." She might go weeks without interacting with another woman at work. So she and a group of friends, including two Tribune journalists, hatched an idea for a magazine for working women.

After four years of effort, the project was abandoned. The "working women's" market was unproven, and financiers were scared to invest. But organizers missed each other, and one suggested forming a larger network. What they called the Old Girls Network grew into the 230-member Chicago Network, an invitation-only group of the city's elite businesswomen.

"Sheli was special, because she had no need of a network to enhance her own career yet saw the need for one for women broadly," said Christie Hefner, one of the network's original members.

When the network launched in 1979, Rosenberg had achieved enough to be deemed one of "the old girls," later called "the old goats." But she hadn't even turned 40.

Zell's persistence pays off

Also in 1979, a short man wearing a lime green jumpsuit came to Schiff to take her to lunch and offer her a job.

It was Zell, who said he monitored her career for 14 years before trying to recruit her. He described Rosenberg as "an ultimate female" who always wore a skirt, and he knew she did not think highly of him and his business partner, Bob Lurie.

"She thought (the job offer) was preposterous, and that we were a bunch of cowboys," Zell said.

Rosenberg declined Zell's offer. Her husband also was adamantly opposed to the move.

"Obviously, I was dead wrong," Burton Rosenberg says now. "But … Sam had been indicted (on tax charges in 1976 related to a real estate deal; the charges were dropped in exchange for testimony). … He didn't have the reputation as a business genius he has now. And I felt to a certain extent he was using her reputation as so pure, and her reputation for integrity, to burnish his image."

But Zell did not give up, and Sheli Rosenberg eventually agreed to form a law firm, first Rosenberg & Perlman and later Rosenberg & Liebentritt, that would serve only Zell and Lurie.

Beginning in the 1980s, Rosenberg helped orchestrate the transformation of Zell and Lurie's numerous investment companies from 100 percent real estate operations to a 50/50 split between real estate and troubled businesses.

"In many respects, she was the holder of the moral code," Zell said. "She was the person everybody looked up to most."

But Rosenberg recalled the gamesmanship that often came with these deals.

On one of them, "the buyer essentially had an option whether to buy (a downtown apartment building), and if they gave us notice, we had to perform in 72 hours or they would have some rights to a penalty," Rosenberg said. "So on Friday afternoon at around 4 o'clock, we got the notice. There was no question they expected us to fall on our faces. … Needless to say, I was really pissed."

But Rosenberg had the home phone number of the title company's chief executive, who marshaled his staff to work all weekend helping prepare the documents.

"On Monday morning, this clown walks into my office with his check, thinking that I couldn't provide the documentation," Rosenberg said. "I will forever enjoy the look that I can, even to this day, see when (I said), 'Got a problem? Here are our documents. We're ready to close. Want to walk over to the title company?' It was wonderful."

That afternoon, Zell and Lurie sent her a dozen roses.

At its peak, Rosenberg & Liebentritt had 35 lawyers and 30 paralegals, Zell said. But the nature of Zell and Lurie's business strategy, often called vulture investing, also caused Rosenberg to be named in numerous lawsuits.

When Lurie died of colon cancer in 1990, leaving a gaping hole in the business operations, Rosenberg came as close to filling his shoes as one could, dropping her legal tasks to oversee companies in which Zell had a controlling interest.

Before long, Zell named Rosenberg chief executive of Equity Group Investments, which housed his central operations. Her office was next to his, separated by a window that, with the push of a button, could be darkened for privacy.

"I remember when we put that in," Zell said. "This was an office where everybody used to just scream at everybody. But as we got bigger, that wasn't as efficient. So we had a window so I could see if she was there and just knock on it when I wanted to talk to her."

During the 1990s, she helped take three of Zell's real estate companies public and raise the Zell/Chilmark Fund, a private equity fund with a value in excess of $1 billion.

Among Zell's legal team, there was little doubt who was in charge.

"She was dealing with some guy at some Southern, big, white-shoe law firm" who was working as outside counsel, said Don Liebentritt, who is now chief restructuring officer at Tribune Co. "He called her 'little lady,' and boy, she just went off.

"That was a pretty short conversation after that, and she was the only one doing the talking."

Peter Fazio, former chairman of Schiff Hardin, laughed at the notion that anyone, even in the 1970s, would have mistaken Rosenberg for anyone but the person in charge.

"She's got presence," he said. "She's not going to be meek and mild, sitting around someplace and being taken for an assistant."

But Rosenberg said it happened.

"A guy once asked me to get him coffee," she said. "I played along and asked him, 'How much cream? How much sugar?' He gave his answers. And then I told him, 'At my hourly rate, that coffee is going to cost you about $270. Is that OK?'"

'I've got to prove myself'

Rosenberg has remained a director of Zell's Equity LifeStyle Properties and also sits on the boards of Ventas, Nanosphere and General Growth Properties.

The Chicago Network now has an organized effort to get its members on corporate boards, powerful posts where women can promote greater pay parity and representation among senior management.

"I served with her on my first non-Playboy, for-profit board, Sealy," Hefner said. "As Sam Zell had a controlling interest in the company, I'm sure that she was responsible for my invitation to join."

Lisa Bisaccia, the senior vice president and human resources chief at CVS Caremark, said Rosenberg and two other female directors would take all of the company's female executives out to dinner after every board meeting.

"A couple years ago, we could all fit at a small table, now it's several tables," Bisaccia said of the 30-plus-member group. "And she would always ask, 'What's going on? What are your career ambitions? How can I help you?' … And she wasn't interested in motherhood and apple pie answers."

In all, Rosenberg has served on about 20 corporate boards. Only a handful of women have achieved as much. Although it shows what's possible, much more is to be done.

Last week, for example, Mayor Rahm Emanuel announced 31 new board members to World Business Chicago, the city's economic development arm. Only one is a woman. According to the Chicago Network's most recent census of Chicago's 50 largest public companies, based on 2009 public filings, 13 of them had no female executive officers and women represented 15 percent of board members.

"There aren't enough successful women, period, so there can't be enough to serve as mentors," said Jill Wine-Banks, who moved to Chicago in 1980 and joined Jenner & Block as a partner. "And now the challenge is that the women who have broken through are being used over and over again. If companies and search firms looked at the broad array of available talent, you would easily have half the board being female."

Rosenberg is cynical about how she reached the boardroom. The invitations come, she said, because she has "proven she doesn't have horns."

"There is a fear that a woman in the boardroom is going to turn meetings into a contested atmosphere," Rosenberg said. "I've proven that I can be in the boardroom with guys and not make them or me sick. That's meant that all of the sudden, I got on everybody's list."

Earlier in the interview, she argued that for all her achievements, she was a "terribly conventional" woman in the 1970s. She made a point of being home for dinner every night and was the primary caregiver. Without a live-in housekeeper, she said, she never would have been able to manage.

"I've never been radical," she said of her approach to gender equality. "I think I've become more obnoxious in this regard, certainly pushier, as I've aged. … I absolutely know I was the benefit of some tokenism, but I also firmly believe you can open the door for me, but once I walk through that door, I've got to prove myself. And if I didn't prove myself, I wouldn't have reaped the benefits."